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Pyranoside‐into‐Furanoside Rearrangement: New Reaction in Carbohydrate Chemistry and Its Application in Oligosaccharide Synthesis Full article

Journal Chemistry: A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765
Output data Year: 2014, Volume: 20, Number: 50, Pages: 16516-16522 Pages count : 7 DOI: 10.1002/chem.201405083
Authors Krylov Vadim B. 1 , Argunov Dmitry A. 1 , Vinnitskiy Dmitry Z. 1 , Verkhnyatskaya Stella A. 1 , Gerbst Alexey G. 1 , Ustyuzhanina Nadezhda E. 1 , Dmitrenok Andrey S. 1 , Huebner Johannes 2 , Holst Otto 3 , Siebert Hans-Christian 4 , Nifantiev Nikolay E. 1
Affiliations
1 Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russian Federation)
2 Division of Pediatric Infectious Diseases, Hauner Children's Hospital, Ludwigs-Maximilian University, Munich (Germany)
3 Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel (Germany)
4 RI-B-NT - Research Institute of Bioinformatics and Nanotechnology, 24118 Kiel (Germany)

Abstract: Great interest in natural furanoside-containing compounds has challenged the development of preparative methods for their synthesis. Herein a novel reaction in carbohydrate chemistry, namely a pyranoside-into-furanoside (PIF) rearrangement permitting the transformation of selectively O-substituted pyranosides into the corresponding furanosides is reported. The discovered process includes acid-promoted sulfation accompanied by rearrangement of the pyranoside ring into a furanoside ring followed by solvolytic O-desulfation. This process, which has no analogy in organic chemistry, was shown to be a very useful tool for the synthesis of furanoside-containing complex oligosaccharides, which was demonstrated by synthesizing disaccharide derivatives α-D-Galp-(1→3)-β-D-Galf-OPr, 3-O-s-lactyl-β-D-Galf-(1→3)-β-D-Glcp-OPr, and α-L-Fucf-(1→4)-β-D-GlcpA-OPr related to polysaccharides from the bacteria Klebsiella pneumoniae and Enterococcus faecalis and the brown seaweed Chordaria flagelliformis.
Cite: Krylov V.B. , Argunov D.A. , Vinnitskiy D.Z. , Verkhnyatskaya S.A. , Gerbst A.G. , Ustyuzhanina N.E. , Dmitrenok A.S. , Huebner J. , Holst O. , Siebert H-C. , Nifantiev N.E.
Pyranoside‐into‐Furanoside Rearrangement: New Reaction in Carbohydrate Chemistry and Its Application in Oligosaccharide Synthesis
Chemistry: A European Journal. 2014. V.20. N50. P.16516-16522. DOI: 10.1002/chem.201405083 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000346055800016
≡ Scopus: 2-s2.0-84924671798
≡ OpenAlex: W2138644438
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